spring of 1851, planking of what was then known as the West Gwillimbury Road began under a funding agreement with the government of Upper Canada. It was completed in October, featuring 3-inch thick planks laid on stringers, and was wide enough for a wagon; the first "paved" road in Simcoe County. Loaded wagons had the right-of-way, and the well-established farmland around Bond Head led to it becoming a major transport route to markets in Toronto. Although initially profitable, the deteriorating condition of the planks, frequent upkeep, and payments to those injured by the condition of the road led to it costing money by 1857. Consequently, in October 1858, Simcoe County council repealed the act that established the plank road, and instructed the county surveyor to remove the planks and level the road. The portion of the plank road between Bradford and Holland Landing followed what is now Bridge Street along the south side of the Ontario, Simcoe and Huron Railway (opened June15, 1853, now the CNR and GO Transit Barrie line) across the Holland River, then crossed to the north side of the tracks, following what is still today known as Toll Road. A part of this, from Barrie Street in Bradford to the south side of the Holland River, was incorporated into Highway 11 on August18, 1920. Highway88 would be established nearly 18years later, when the remainder of the former plank road between Bradford and Bond Head became a provincial highway on April13, 1938. While still a dirt road, it was improved to a gravel surface the following year. Planning for a new "superhighway" between Toronto and south of Barrie was carried out between 1944 and 1947, with construction beginning later that year. When Highway400 fully opened to traffic on July1, 1952, a cloverleaf interchange with Highway88 was included. It was one of the last remaining in Ontario when the loops were removed in 2011, converting it to a diamond interchange. Highway88 was paved in its entirety in 1956. As part of a series of budget cuts initiated by premier Mike Harris under his Common Sense Revolution platform in 1995, numerous highways deemed to no longer be of significance to the provincial network were decommissioned and responsibility for the routes transferred to a lower level of government, a process referred to as downloading. Highway88 was downloaded entirely on January1, 1998, and transferred to Simcoe County, which designated it as